Water → 2-Bromo-4-ethylsulfonyl-1-methoxybenzene

HRID 518301Notes

Reaction equation

HRID 518301 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([S:8]([CH2:11][CH3:12])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1F.C[O-].[Na+].O.[C:18](OCC)(=[O:20])C>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([S:8]([CH2:11][CH3:12])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:20][CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl Acetate2×HCID 10942334Sodium MethoxideHCID 585219752-Bromo-4-(ethylsulfonyl)-1-fluorobenzene

Product 1

HCID 109788092-Bromo-4-ethylsulfonyl-1-methoxybenzeneYield 79.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-bromo-4-ethylsulfonyl-1-fluorobenzene (0.6 g, 2.25 mmol) and sodium methoxide (1.2 g, 22.2 mmol) in THF (20 mL) was stirred at room temperature for 18 h. Water (30 mL) was added and extractive work up with ethyl acetate followed by silica gel chromatography (PE:EA=10:1 to 1:1) gave the title compound (0.5 g, 79.4%) as a yellow solid. 1H NMR (CDCl3, 400 MHz) δ 8.08 (d, J=2.4 Hz, 1H), 7.87-7.84 (dd, J1=8.6 Hz, J2=2.4 Hz, 1H), 7.04 (d, J=8.8 Hz, 1H), 3.99 (s, 3H), 3.11 (q, J=7.4 Hz, 2H), 1.30 (t, J=7.4 Hz, 3H).

Sources & evidence

ORD record
ord-60ba37292d3d4618abe4ca751d37609a
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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